Boyfriend lacking penile sensitivity? (HELP!)

He has no trouble at all receiving an erection, he does orgasm most of the time during sex, however I am concerned about his penis sensitivity. He's always masturbated by rubbing his shaft against his bed in a rough fashion. We were both virgins before we've had sex, though he's been masturbating frequently in this manner for many years beforehand. He said he's only been able to get off once or twice by hand. I'm concerned because the way he masturbates is very dry and rough. I'm afraid his nerves have been damaged. He usually can't orgasm unless we do it doggie-style because he said his penis scrapes against my wall more this way. For the most part, he doesn't like how warm, soft, wet, tight, my vagina feels. o-o I am also unable to get him off orally or manually, despite being able to get my previous partners off this way (and they told me I was excellent). Additionally, I invited him to try anal. He got it in about halfway until I requested he stopped. I asked him how it felt and he said he felt nothing. Of course I love him for who he is, and I don't discuss it much with him as to not stress him out. But it does need to be discussed and I want to know if there's anything we could do to restore the sensitivity of his penis. He is circumsized, healthy, and of average size. He seems extremely attracted to me and I try as hard as I possibly can, providing him with all he could want, yet I feel incompetent because my vagina isn't hard and dry. o_o Help us!